Can this dent in my upper cheek be filled with filler? (Photos)

Interesting problem. I have seen this type of dimple develop on a family friend's child. I remember distinctly, that the child fell hard and hit his cheek on a sharp coffee table corner and developed an initial facial indentation, which quickly filled in with a hematoma/bruise. It looked smooth initially, then later, developed into a slight indentation which worsed when the child smiles.
Reverse engineering what probably happened is that the coffee table corner indented the skin and may have caused a tear in the fat underneath, without breaking the skin. The fat healed but with a separation between the sides of the fat. The scar tissue in the center of the dent may be healed against some deeper muscles/layers, to cause the worsening when smiling.
When you smile the lifting of the corners of the mouth causes the cheek apples to mound up and bulge. Since there is a separation of the fat and scar tissue at the site of the dent, the fat around the dent bulges more, but the scar tissue which is not as spongy as fat, does not bulge out like the surrounding fat, thus causing the deepening of the dimple when you smile.
The filler may hide the "resting" indentation, but I suspect it will still indent and cause the "dimple" when you smile. There is a procedure called "subcision" which releases the skin from underlying scar tissue which is "tethering" the skin down. Subcision is typically used for acne scars and cellulite improvement, but these are indentations which are there "at rest" and we do not have to deal with an a "dynamic" indentation.
The reason for the deep dive is to explain what may be the cause the problem. Filler/subcision may reduce the resting indentation, but I am not sure what will happen when you smile hard.
Best,
Dr. Yang

I appreciate your question and your photos. An indentation like this may be treated by some well-placed filler or by releasing the tissue, depending on the cause of the indentation. I recommend getting an assessment with a board-certified facial plastic surgeon who can determine the cause of the indentation and create the best treatment plan for you.

The best results are usually achieved using a combination of treatments. Subscision of the scar, followed by dermal fillers or dermal grafting would improve the appearance quite a bit. Laser may or may not be required afterwards for skin resurfacing.